Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation

Mingyu Niu; Zhengming Yin; Hua Fu; Yuyang Jiang; Yufen Zhao

doi:10.1021/jo800279j

Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation

J Org Chem. 2008 May 16;73(10):3961-3. doi: 10.1021/jo800279j. Epub 2008 Apr 12.

Authors

Mingyu Niu¹, Zhengming Yin, Hua Fu, Yuyang Jiang, Yufen Zhao

Affiliation

¹ Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, PR China.

PMID: 18407687
DOI: 10.1021/jo800279j

Abstract

We have developed a convenient and efficient method for coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation. The protocol uses CuBr as the catalyst, NBS as the free radical initiator, CH(3)CN as the solvent, and the alkynylation was selectively performed on the methyl of tertiary aliphatic amines at 80 degrees C. This is an economical and practical method for the synthesis of propargylamines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemical synthesis*
Alkynes / chemistry*
Amines / chemical synthesis*
Amines / chemistry*
Catalysis
Copper / chemistry*
Molecular Structure
Stereoisomerism

Substances

Alkynes
Amines
Copper